Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
  • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
  • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
  • B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
  • B01J41/08—Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
  • B01J41/12—Macromolecular compounds
  • B01J41/13—Macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
  • B01J47/00—Ion-exchange processes in general; Apparatus therefor
  • B01J47/12—Ion-exchange processes in general; Apparatus therefor characterised by the use of ion-exchange material in the form of ribbons, filaments, fibres or sheets, e.g. membranes
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
  • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
  • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
  • C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
  • C08G65/4031—(I) or (II) containing nitrogen
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
  • C08J5/20—Manufacture of shaped structures of ion-exchange resins
  • C08J5/22—Films, membranes or diaphragms
  • C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
  • C08J5/2218—Synthetic macromolecular compounds
  • C08J5/2256—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions other than those involving carbon-to-carbon bonds, e.g. obtained by polycondensation
• • C—CHEMISTRY; METALLURGY
  • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
  • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
  • C25B13/00—Diaphragms; Spacing elements
  • C25B13/04—Diaphragms; Spacing elements characterised by the material
  • C25B13/08—Diaphragms; Spacing elements characterised by the material based on organic materials
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
  • H01M8/00—Fuel cells; Manufacture thereof
  • H01M8/10—Fuel cells with solid electrolytes
  • H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
  • H01M8/1018—Polymeric electrolyte materials
  • H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
  • H01M8/1025—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having only carbon and oxygen, e.g. polyethers, sulfonated polyetheretherketones [S-PEEK], sulfonated polysaccharides, sulfonated celluloses or sulfonated polyesters
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
  • H01M8/00—Fuel cells; Manufacture thereof
  • H01M8/10—Fuel cells with solid electrolytes
  • H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
  • H01M8/1018—Polymeric electrolyte materials
  • H01M8/1069—Polymeric electrolyte materials characterised by the manufacturing processes
  • H01M8/1072—Polymeric electrolyte materials characterised by the manufacturing processes by chemical reactions, e.g. in situ polymerisation or in situ crosslinking
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
  • C08J2371/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
  • C08J2371/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
  • H01M2300/00—Electrolytes
  • H01M2300/0017—Non-aqueous electrolytes
  • H01M2300/0065—Solid electrolytes
  • H01M2300/0082—Organic polymers
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
  • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
  • Y02E60/30—Hydrogen technology
  • Y02E60/50—Fuel cells
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
  • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
  • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

Definitions

• the present invention provides compounds, especially polymeric compounds, having some kind of spiro or piperidine structural unit, a process for preparation thereof and for the use thereof, especially as anion-conducting membranes.
• Polymeric ion-conducting membranes have long been known.
• the membranes described in WO 2005/045978 A2, US 2009325030 A1 and US 20040121210 A1 are based on a highly fluorinated polymer backbone.
• anion-conducting membranes are produced, in which a porous film is impregnated with a mixture of various monomers having vinyl groups, at least one of which has a halogen group (chlorine group), the surfaces of the porous film are each covered with a polyester film and then a thermal polymerization is conducted. The material thus obtained is then treated with trimethylamine or methyl iodide and then with NaOH. In EP 2296210 A1, the treatment with trimethylamine is followed by a treatment with Na 2 CO 3 .
• anion-conducting membranes are obtained by the curing of a polymer solution containing polymers that have been obtained by chloromethylation of polysulfones and subsequent treatment with trimethylamine.
• CN 104829814 B discloses a polymer containing a quaternized piperidine group, a preparation method thereof, an anion exchange membrane, and a preparation method thereof.
• the main chain of the polymer is mainly composed of benzene rings, and the prepared anion exchange membrane has a good mechanical property.
• the quaternized piperidine group (cation group) in the side chain has a strong alkali resistant performance.
• the synthesis method of the polymer is simple, the content of the ion groups is controllable, and the polymer can be used to produce anion exchange membranes having the advantages of good mechanical property, high conductivity, and strong alkali resistant performance.
• WO 2017172824 A1 discloses poly(aryl piperidinium) polymers which have an alkaline-stable cation, piperidinium, introduced into a rigid aromatic polymer backbone free of ether bonds. Hydroxide exchange membranes or hydroxide exchange ionomers formed from these polymers exhibit superior chemical stability, hydroxide conductivity, decreased water uptake, good solubility in selected solvents, and improved mechanical properties in an ambient dry state as compared to conventional hydroxide exchange membranes or ionomers. Hydroxide exchange membrane fuel cells comprising the poly(aryl piperidinium) polymers exhibit enhanced performance and durability at relatively high temperatures.
• T. H. Pham, J. S. Olsson and P. Jannasch developed poly(arylene alkylene)s with pendant N-spirocyclic quaternary ammonium cations for anion exchange membranes and hydroxide ion conducting poly(terphenyl alkylene)s functionalized with piperidine-based quaternary ammonium cations and there synthesis (T. H. Pham, J. S. Olsson, P. Jannasch, J. Mater. Chem. A, 2018, 6, 16537-16547 and T. H. Pham, J. S. Olsson, P. Jannasch, J. Mater. Chem. A, 2019, 7, 15895-15906).
• the problem addressed by the present invention was that of providing alternative compounds suitable as or for production of anion-conducting polymers.
• the present invention likewise provides a process for preparing such compounds and for the use thereof as anion-conducting membranes, and also these membranes themselves.
• the polymers according to the invention have the advantage that they can be prepared in a simple manner.
• the membranes produced therefrom have the advantage that they have very high mechanical stability and low swelling characteristics combined with high dimensional stability. In addition, the membranes exhibit quite high anion conductivities.
• the present invention provides compounds, containing at least one unit of the formula (I)
• X being a structure element comprising a nitrogen atom with a positive charge bonded to C 1 and C 2 and bonded via two bonds to one or two hydrocarbon radical(s) comprising 1 to 12, preferably 1 to 6, more preferably 1 or 5 carbon atoms
• Z being a structure element comprising a carbon atom being bonded to C 3 and C 4 and at least one aromatic 6-ring directly bonded to one of the oxygen atoms, wherein the aromatic rings might be substituted with one or more halogen and/or one or more C 1 - to C 4 -alkyl radicals.
• the compound of the present invention is represented by formula (Ia) or (Ib)
• Y unsame or different halogen, preferably F, M being an integer from 1 to 500, preferably 5 to 250
• X being a structure element comprising a nitrogen atom with a positive charge bonded to C 1 and C 2 and bonded via two bonds to one or two hydrocarbon radical(s) comprising 1 to 12, preferably 1 to 6, more preferably 1 or 5 carbon atoms
• Z being a structure element comprising a carbon atom being bonded to C 3 and C 4 and at least one aromatic 6-ring directly bonded to one of the oxygen atoms, wherein the aromatic rings might be substituted with one or more halogen and/or one or more to C 1 - to C 4 -alkyl radicals.
• the structure element X preferably represents a unit of formula (IIa) or (IIb)
• the structure element X present in the compound of the present invention represents in more than 50%, preferably in more than 75%, and most preferred in more than 90% of its occurrence a unit of formula (IIa) or (IIb).
• the occurrence can be determined for example by 1 H-NMR and/or 13 C-NMR.
• the structure element Z preferably represents a unit of formula (IIIa)
• R 1 , R 2 , R 3 , and R 4 being the same or different —H or an alkyl group having from 1 to 4 carbon atoms, R 1 , R 2 , R 3 and R 4 each preferably being a methyl or tert-butyl group, more preferably being a methyl group.
• the compound of the present invention is preferably represented by at least one of formulas (IVa) to (IVd),
• M a and M b being an integer of from 1 to 500, preferably of from 5 to 250, and wherein the aromatic rings might further be substituted with one or more halogen and/or one or more C 1 - to C 4 -alkyl radicals.
• Most preferred compounds of the present invention are those, where the aromatic rings in the compounds of formula (I), (Ia), (Ib), (IVa), (IVb), (IVc), and (IVd) are not further substituted with one or more halogen or one or more C 1 - to C 4 -alkyl radicals.
• the compounds according to the invention can be obtained, for example, by the process according to the invention described hereinafter.
• the process of the present invention is characterized in that it comprises a step in which a compound of the formula (V)
• this reaction step is carried out at a temperature of from 100 to 300° C., more preferably at a reaction temperature of from 125 to 175° C. Most preferably the reaction step is carried out at a temperature where the reaction mixture is boiling, preferably while stirring.
• the reaction step is most preferably carried out under an inert gas atmosphere, preferably a nitrogen atmosphere. At the top of the reaction vessel, any methanol and/or water formed is preferably removed.
• the reaction step is preferably carried out in the presence of K 2 CO 3 .
• the reaction step is preferably carried out in the presence of an organic solvent.
• an organic solvent Preferably dimethylacetamide is used as a solvent.
• the process according to the invention comprises a step where an alkylating reagent, preferably a methylating reagent, is used.
• the preferred methylating agent used is iodomethane.
• the aromatic rings in the compounds of formula (V), (VIa), and (VIb) are not further substituted with one or more halogen or one or more C 1 - to C 4 -alkyl radicals.
• the compounds of the present invention might be used for different purposes.
• the compounds of the present invention are polymers and are used as anion-conducting membranes or for the production of anion-conducting membranes.
• the compounds of the present invention are used for the production of a component, which is used in an electrochemical process, preferably selected from electrolysis, electrodialysis and fuel cell technology.
• Another aspect of the present invention are processes for the production of anion-conducting membranes and for the production of components, which can be used in an electrochemical process, preferably selected from electrolysis, electrodialysis and fuel cell technology, characterized in that a compound according to the present invention is applied.
• Another aspect of the present invention is therefore an electrolyzer, characterized in that it includes a compound according to the present invention as described above.
• Synthesis was performed in a 500 mL three-necked flask with oil bath, mechanical stirrer, a packed column with distillation head cooler with adjustable return ratio and condensate removal.
• 0.09 mol (30.51 g) of N-Methyl-4,4-Bis (3′,5′-Dimethyl, 4′-Hydroxyphenyl)-Piperidine, 0.09 mol (19.62 g) of 4,4′-Difluorobenzophenone, 105 g of dimethylacetamide and 0.135 mol of finely ground K 2 CO 3 were mixed under nitrogen atmosphere over 1 hour at room temperature. Afterwards the temperature of the oil bath was increased to 235° C. leading to boiling of the reaction mixture.
• Example 3 Quaternization of Piperidine Containing Polymer from Example 2
• Example 4 Membrane Casting of Piperidine Containing Polymer from Example 3
• the solution of the quaternized polymer from Example 3 was directly used for preparation of the membrane.
• the required amount of polymer solution was taken up with a syringe and applied directly through a 0.45 ⁇ m PTFE filter on a glass plate preheated to 40° C.
• an applicator with doctor blade was automatically pulled over the glass plate at a speed of 5 mm/s.
• the applied wet layer was pre-dried for 12 hours under nitrogen atmosphere at room temperature and then dried for 6 hours at 60° C. under vacuum.
• reaction products were cooled to room temperature, precipitated KBr was separated by filtration and the solution was concentrated on a rotary evaporator. During concentration process additional amount of KBr crystallizes and was filtered off. The filtrate solidified at temperature below 80° C., was filtered and used without further purification as one of educts for synthesis of spiro containing monomer (VIa).
• Synthesis was performed in a 100 mL three-necked flask with oil bath, mechanical stirrer, a packed column with distillation head cooler with adjustable return ratio and condensate removal.
• 0.01 mol (4.89 g) of 3,3-bis(4-hydroxy-3,5-dimethylphenyl)-6-azaspiro [5.5]undecane-6-ium methane sulfonate, 0.01 mol (2.18 g) of 4,4′-Difluorobenzophenone, 15 g of dimethylacetamide and 0.0125 mol (1.73 g) of finely ground K 2 CO 3 were mixed under nitrogen atmosphere over 1 hour at room temperature. After that, the temperature of the oil bath was increased to 235° C.
• Example 7 Membrane Casting of Spiro Containing Polymer from Example 6
• Step 1 In a 100 ml three-necked flask with magnetic stirrer, heating and reflux condenser, 0.02 mol (6.72 g) 4,4′-(Hexafluoroisopropylidene)diphenol, 0.018 mol (3.924 g) 4,4′-Difluorobenzophenone were dissolved in 24 g dimethylformamide. After adding 0.0225 mol (3.1 g) milled K 2 CO 3 , all educts were refluxed for 4 hours and then cooled to room temperature under nitrogen atmosphere.
• Step 2 In a 250 ml three-necked flask with mechanical stirrer, heating, column with distillate removal head 0.02 mol (9.78 g) of spiro containing monomer (VIa) from Example 5, 0.022 mol (4.796 g) 4,4′-Difluorobenzophenone, 0.0225 mol (3.1 g) milled K 2 CO 3 were mixed in 35 g dimethylformamide and slowly heated to boiling. As a result, a sparingly soluble precipitate was formed and was resolved completely in the course of reaction. Water formed during the reaction was removed at the column head. Mixture of educts was refluxed for 15 hours and then cooled to room temperature under nitrogen.
• Step 3 The reaction mass of Step 1 was slowly added into the reaction mass of Step 2 and 25 g dimethylformamide were added to this mixture.
• the apparatus was purged with nitrogen and boiled for 6 hours at reflux and while stirring.
• the solution was cooled to room temperature under nitrogen atmosphere.
• Example 9 Membrane Casting of Spiro Containing Block-co-Polymer from Example 8
• the applied wet layer was pre-dried for 12 hours under nitrogen at room temperature and then dried for 6 hours at 60° C. under vacuum.
• the membranes prepared in Examples 4, 7, and 9 respectively were ion-exchanged: Samples of the membranes were placed in aqueous 1 M KOH solution for 24 hours at 60° C. Afterwards the membrane samples were rinsed off with deionized water and placed in fresh portions of the deionized water 3 times for 1 hour each at 60° C. Subsequently, the membrane samples were stored in a fresh portion of the deionized water overnight at room temperature.
• the in-plane ionic conductivity of ion-exchanged membrane samples from Example 10 were measured by means of impedance spectroscopy (EIS) in a conventional 4-electrode arrangement.
• the membrane sample was mounted in a commercial BT-112 cell (Bekk Tech LLC), so that the two outer Pt wires were placed under the sample and the two midpoint Pt wires above the sample.
• the BT-112 cell was mounted between 2 PTFE plates and filled with deionized water. The temperature of the deionized water was controlled by a water bath and deionized water was pumped permanently through the cell.
• the calculation of the membrane resistance (R membrane ) was carried out by fitting acquired EIS spectrum using a widely used R (RC) Randles equivalent circuit.
• ⁇ L /(R membran *A ) (1)
• L is the distance between Pt wires (5 mm)
• A is the area of the membrane sample between the two outer Pt wires.
• Ion-exchanged membrane samples from Example 10 (3 samples per membrane tested) were used for measurement of water uptake. All samples were dried for 24 hours in a vacuum oven at 40° C. and 25 mbar, then cooled in a desiccator to room temperature and weighted. For the measurement of the water uptake, membrane samples were stored for 24 hours in deionized water at 25° C. Subsequently, the weight of each sample was determined again. For this purpose, adhering water was removed from the membrane with the aid of a filter paper. Each measurement was repeated 3 times and a mean ⁇ standard deviation was calculated.
• Ion-exchanged membrane samples from Example 10 (3 samples per membrane tested) were used for the measurement of dimensional stability. All samples were dried for 24 hours in a vacuum oven at 40° C. and 25 mbar, then cooled in a desiccator to room temperature. Such parameters as the sample length, the sample width and the sample thickness were determined. To determine the swelling behavior, membrane samples were stored for 24 hours in deionized water at 25° C. Subsequently, the sample length, the sample width and the sample thickness were determined again. For this purpose, adhering water was removed from the membrane with the aid of a filter paper. Each measurement was repeated 3 times and a mean ⁇ standard deviation was calculated.
• DS ( x wet ⁇ x dry ) /x dry *100% (3) with x wet the length, width or thickness of the sample after swelling and x dry the dry length, dry width or dry thickness of the sample.
• Ion-exchanged membrane samples from Example 10 were stored for 24 in deionized water at 25° C. Before the sample was installed in the measuring system (DMA 8000 with water bath), the width and thickness of each membrane sample were determined. Each measurement was repeated 3 times and a mean ⁇ standard deviation was calculated. DMA measurement was performed as follows: —membrane sample is installed between two perpendicular braces with a static preload. In order to apply a static preload to the sample, the distance between the clamps (also referred to as free path length l) is reduced by about 1 mm during installation. The specimen is fixed between the two staples and then the original free path length is restored, stretching the specimen.
• the entire test setup is immersed in deionized water in a heated water bath so that the sample is completely surrounded by water.
• the measuring procedure involves the examination of the sample in a temperature range between room temperature (25° C.) and 90° C. at an applied heating rate of 2 K/min.
• membrane sample is continuously loaded sinusoidally with an elongation c of 0.1% at a frequency of 1 Hz.
• Via a force sensor the voltage required for the given strain is detected.
• the membranes according to the invention show a DMA value that is at least 5 times higher than the DMA value of the prior art membranes. It is therefore possible to produce thinner membranes with equal mechanical stability.

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